Head Of Digital Enablement And Assurance

Steadfast Group is the largest general insurance broker network and the largest underwriting agency group in Australasia with growing operations internationally. We were founded on the belief that a network of brokers would be stronger together, and this idea has been the backbone of our culture ever since. We believe that none of us is as good as all of us.
At Steadfast, we take pride in the diverse mix of individuals and skill sets within our organisation. Our team members collaborate across various business units to not only bolster our broker network but also to pioneer the innovative thinking, systems, and technologies that will propel the insurance sector into the future.
We are leaders of the general insurance broking and underwriting industry, and we lead from the front.
About the opportunity
The Head of Digital Enablement & Operational Assurance is a critical leadership role responsible for advancing Steadfast Group's digital workplace strategy and operational maturity agenda. Working in close partnership with the CTO and their leadership team, this role will drive enterprise-wide digital adoption, operationalise technology solutions, embed data governance, and build operational resilience through robust frameworks and continuous improvement initiatives.
In addition, this role will lead Operational Assurance practices in collaboration with the GM of Risk & Compliance, ensuring consistent operational execution across Group functions and Subsidiary businesses. The position also oversees head office budget management and performance, strengthening commercial discipline to support the Group in meeting market expectations and growth objectives.
Responsibilities
Lead the implementation and optimisation of digital workplace solutions, including enterprise platforms and automated workflowsDevelop and manage a Group-wide Digital Roadmap to prioritise tooling and innovation initiativesDrive scalable AI adoption to replace manual processes and enhance productivityDefine strategy and governance for low-code/no-code tools (e.g. Power Apps) in collaboration with Technology teamsOversee Group budget and FTE management processes, embedding commercial disciplineDesign and deliver enterprise dashboards to enable data-driven decision-makingLead the development of operational policies and data governance frameworksChampion continuous improvement and knowledge management across Group functions
Skills and Knowledge
At least 10 years' experience in digital workplace transformation, operational governance, or enterprise enablement roles.Strong understanding of enterprise tooling, workflow automation, and service management platforms. (Microsoft Sharepoint experience would be preferable)Experience with AI education, enablement & adoption. We have a Director of AI, however we're looking for a leader who can take our policies and frameworks and execute them across the business and produce a 'Playbook' for other subsidiaries to do so.Experience with rolling out and governing low-code platforms (e.g., Power Apps, Power Automate), and digital workplace solutions.Demonstrated experience in financial and commercial management at a Group or enterprise level to support the maturing of reporting and managing monthly, quarterly and annual financial cycles.Deep knowledge of governance frameworks including BCP, data governance, and operational policy development.Strong problem-solving and continuous improvement mindset with the ability to operationalise strategy.Exceptional stakeholder engagement and communication skills, with a track record of influencing at senior levels.
Benefits
As a valued member of the Steadfast team, you'll enjoy a comprehensive array of benefits tailored to support your professional and personal well-being. Joining Steadfast means gaining access to:
Flexible working arrangements to help you balance work and home life.Career advancement opportunities and professional development through training programs, mentorship initiatives, and tuition reimbursement. We also partner with ANZIIF for accreditation and qualifications.Free company provided Life, Temporary Permanent Disablement, Salary Continuance and Travel insurances, plus access to other discounted insurances.An expansive Health and Wellbeing program, which includes free annual health checks, free annual skin checks, Flu shots, holistic support and advice, discounted gym membership, and confidential counselling.Discounts on travel, hotels, hire cars, electronic and vehicle packages through our various partners.Working in a vibrant and collegiate culture where you are a person, and your contribution is valued.
About us
Our purpose is to create solutions designed to help our businesses and network achieve better outcomes for their clients and the communities we serve from our people, processes and culture.
We are committed to providing a workplace where people feel they can bring their whole self to work. We aim to create a diverse work environment in which everyone is treated fairly and with respect and where everyone feels responsible for the reputation and performance of Steadfast.
We are strong supporters of Aboriginal and Torres Strait Islander peoples, businesses and communities through our Reconciliation Action Plan. We are also passionate about the environment, diversity, equity and inclusion, and love to give back to charities through the Steadfast Foundation.
We are proud of our Family Friendly Accreditation as well as and our Work180 Endorsement. We are major sponsors of Women in Insurance, Young Insurance Professionals, Head over Heels, the Dive In festival and are active members of Champions of Change.
To apply
We are always on the lookout for great talent, if you are interested in a confidential conversation regarding career opportunities, please email
We believe that our people are our greatest asset. Our people are chosen for their personalities, their ethics and professional qualities without any exclusion, preferential treatment, or discrimination. We are proud to be an equal opportunities employer and do not discriminate by reason of age, gender, gender identity, race, sexual orientation, nationality, religion or disability or any other difference. We encourage applications from all individuals and will provide appropriate assistance for candidates with disabilities or special needs throughout the recruitment process upon request.